Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 363 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 523 departures starting between May 2024 and April 2027.
Filter Results
Departures
Show More...
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$1,600pp
$37,350pp
Countries
Show More...
Filter Results
363 Cruises (523 Cruise Departures)
Cruise

32 Days (31 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 January 2025
Countries Visited: USA, Mexico, Bahamas, Saint Barthelemy (+9 more), Guadeloupe, Saint Vincent, Martinique, Antigua and Barbuda, Virgin Islands, Cayman Islands, Costa Rica, Panama, Colombia
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$21,829
SUITE
$26,730
From 21,829
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 24 January 2025
Countries Visited: USA, Saint Barthelemy, Guadeloupe, Saint Vincent (+3 more), Saint Lucia, Antigua and Barbuda, Virgin Islands
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$9,172
SUITE
$11,192
From 9,172
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 17 December 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Guadeloupe, Saint Lucia, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,467
SUITE
$10,833
Save 2,053
From 6,467
Cruise

10 Days (9 Nights) Bridgetown to Tampa
Cruise Line: Oceania Cruises
Departure: 22 February 2026
Countries Visited: Barbados, Aruba, Jamaica, Mexico (+1 more), USA
Exclusive Deal
INSIDE
$4,189
OCEANVIEW
$4,882
BALCONY
$6,485
SUITE
$8,396
Save 2,031
From 4,189
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 20 December 2024
Countries Visited: USA, Anguilla, Guadeloupe, Virgin Islands (+2 more), Saint Martin, Puerto Rico
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$7,217
SUITE
$8,776
From 7,217
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 05 March 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+6 more), Grenada, Saint Vincent, Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,132
SUITE
$15,310
Save 4,228
From 14,132
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 11 December 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+3 more), Martinique, Antigua and Barbuda, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,883
SUITE
$10,358
Save 6,277
From 8,883
Cruise

8 Days (7 Nights) Marigot to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departures: Mar 2025 to Apr 2025
Countries Visited: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+2 more), Antigua and Barbuda, Guadeloupe
Exclusive Savings
INSIDE
-
OCEANVIEW
$10,526
BALCONY
$14,162
SUITE
$15,200
Save 204
From 10,526
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 07 November 2024
Countries Visited: USA, Honduras, Belize, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$7,690
Save 3,120
From 7,690
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 14 March 2026
Countries Visited: USA, Mexico, Guatemala, Belize (+3 more), Honduras, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,956
SUITE
$12,877
Save 6,294
From 10,956
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Departures: Nov 2024 to Mar 2025
Countries Visited: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,420
SUITE
$6,272
From 5,420
Cruise

11 Days (10 Nights) Bridgetown to Miami
Cruise Line: Oceania Cruises
Departure: 12 December 2024
Countries Visited: Barbados, Grenada, Saint Vincent, Saint Lucia (+6 more), Dominica, Antigua and Barbuda, Saint Barthelemy, Puerto Rico, Dominican Republic, USA
Cabin Upgrade Offer
INSIDE
$3,427
OCEANVIEW
$3,427
BALCONY
$4,110
SUITE
$5,714
From 3,427
Cruise

10 Days (9 Nights) Cartagena to Bridgetown
Cruise Line: Silversea
Departures: Dec 2025 to Mar 2026
Countries Visited: Colombia, Aruba, Bonaire, Curacao (+3 more), Saint Lucia, Saint Vincent, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,504
BALCONY
$10,296
SUITE
$15,048
From 9,504
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Feb 2026
Countries Visited: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Virgin Islands, Sint Maarten, Martinique, Saint Vincent, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,858
SUITE
$15,665
From 9,858
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 15 March 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+1 more), Virgin Islands
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,489
SUITE
$9,128
From 7,489
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 24 February 2026
Countries Visited: USA, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+1 more), Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,341
SUITE
$6,519
From 5,341
Cruise

22 Days (21 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departure: 01 February 2025
Countries Visited: Barbados, Curacao, Bonaire, Aruba (+9 more), Colombia, Dominican Republic, Antigua and Barbuda, Martinique, Saint Lucia, Guadeloupe, Virgin Islands, Saint Kitts and Nevis, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$17,438
SUITE
$32,837
From 17,438
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Mar 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+3 more), Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$6,149
SUITE
$11,366
From 6,149
Cruise

20 Days (19 Nights) Miami to Bridgetown
Cruise Line: Oceania Cruises
Departure: 08 January 2026
Countries Visited: USA, Mexico, Belize, Honduras (+9 more), Aruba, Curacao, Trinidad and Tobago, Grenada, Saint Lucia, Saint Vincent, Dominica, Martinique, Barbados
Exclusive Deal
INSIDE
$8,808
OCEANVIEW
$9,719
BALCONY
$12,778
SUITE
$16,461
Save 2,062
From 8,808
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 14 November 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,475
SUITE
$10,436
Save 3,435
From 9,475
Cruise

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 21 February 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+2 more), Trinidad and Tobago, Barbados
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,158
SUITE
$6,272
From 5,158
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 20 December 2025
Countries Visited: USA, Aruba, Bonaire, Curacao (+5 more), Grenada, Saint Lucia, Guadeloupe, Saint Kitts and Nevis, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$12,134
SUITE
$14,352
Save 7,056
From 12,134
Cruise

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Ray
Departures: Dec 2025 to Mar 2026
Countries Visited: USA, Turks and Caicos Islands, Virgin Islands, Saint Kitts and Nevis (+2 more), Saint Martin, Puerto Rico
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$10,593
From 10,593
New ReleaseCruise

7 Days (6 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Departure: 07 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$4,252
BALCONY
-
SUITE
$5,430
Save 3,543
From 4,252
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 14 January 2025
Countries Visited: USA, Virgin Islands, Saint Barthelemy, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,608
SUITE
$5,371
From 4,608
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 28 January 2026
Countries Visited: USA, Mexico, Honduras, Guatemala (+3 more), Belize, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,628
SUITE
$12,172
Save 2,062
From 7,628
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 08 January 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
$3,190
OCEANVIEW
$3,645
BALCONY
$4,863
SUITE
$6,309
Save 2,020
From 3,190
Cruise

19 Days (18 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 09 March 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Barbados (+6 more), Grenada, Dominica, Saint Barthelemy, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$11,626
SUITE
$16,071
Save 2,094
From 11,626
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 07 December 2025
Countries Visited: USA, Aruba, Curacao, Grenada (+2 more), Saint Lucia, Puerto Rico
Exclusive Deal
INSIDE
$3,500
OCEANVIEW
$4,113
BALCONY
$6,103
SUITE
$8,499
Save 2,020
From 3,500
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 20 March 2025
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$4,991
SUITE
$7,040
Save 2,039
From 4,991
Results: 91-120 of 363

No Results found. Try changing your search filters.

Caribbean & Bahamas Cruises